Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

On day 2 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 1 night and discover all the best things to see and do in the area.

One of the most iconic places you can visit today in Milan is Navigli. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Today’s agenda in Milan includes a church, a shopping mall, a castle, a park, a public square and much more! Duomo Di Milano Museum is must-visit church and a great starting point for the day. Next, continue your journey to Galleria Vittorio Emanuele Ii, a famous shopping mall, located just a leisurely stroll away. Next, head to Sforzesco Castle Art Library, a culturally significant castle, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. When you're ready, let your sightseeing route take you to the top-rated Parco Sempione. If you’re looking for more, Piazza Gae Aulenti is also an interesting attraction that is worthwhile a visit.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Bring home unique finds from Milan's bustling shopping hub, Galleria Vittorio Emanuele II. Enjoy a leisurely exploration of unique high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Galleria Vittorio Emanuele II offers plenty of options, including primary services, unique landmarks, and community events.

As you explore more of Milan, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Savor the flavors at Dessert Bar Milano, a top pick for dinner tonight. Alternatively, Radisson Blu Hotel Milan beckons with its unique menu offerings. Also, consider Ristorante Qui Si Mangia. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

Keep the evening going at Kilburn Cocktail Bar Milano, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Frida, which offers a similarly pleasant setting and great drinks. Another option is The Friends Pub Milano, which provides an inviting environment for unwinding after a busy day out.

Say good night to Milan and look forward to another great day of your road trip in Italy!

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 4 vibrant destinations - Como, Rogaro, Lenno, and Colonno. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Como. You will spend 1 night here for some well-deserved relaxation.

Start your adventure at Basilica Di San Fedele. This intriguing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Saint Mary Assunta Cathedral, a must-see church in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Villa Carlotta (lake Como). This locally appreciated museum offers an enriching experience. Conclude your self-guided sightseeing tour with a visit to Greenway Del Lago Di Como. These sights offer a fulfilling end to a perfect day.

When you’re done exploring for the day, you’ll drive to your hotel in Como. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Como. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Savor the flavors at L’Antica Trattoria, a top pick for dinner tonight. Alternatively, Gesumin Restaurant beckons with its unique menu offerings. Also, consider Pronobis. With its consistent customer satisfaction, it’s an excellent option for dining in Como tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Fresco Cocktail Shop, known for its inviting atmosphere. Bar Il Cortiletto is another great option if you’re looking for a place to get the night started. Similarly, Bar Pinocchio provides a great setting to enjoy the night away.

Savor another day of unforgettable experiences in Italy!

On day 4 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Verona. In the evening, you’ll end up in Verona, where you will stay for 1 night.

Prepare for a day full of family-friendly attractions, romantic experiences, and natural wonders. When you’re ready, kick off your sightseeing adventure at Giusti Garden. This frequently visited botanical garden is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Ponte Pietra, one of the city’s best highlights.

Next, check out Piazza Dei Signori, one of the most intriguing places to see in Como. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Delle Erbe. Wander around and soak in the visually striking atmosphere this public square offers. Then, head to Castelvecchio Museum, a top-rated museum that adds another dimension to your day. Finally, visit the world-famous Verona Arena, the last of our attraction recommendations for today.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Verona. Verona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Verona. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Have a fantastic dining experience at La Griglia, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Vecio Macello offers an enticing alternative with its varied menu. Additionally, Via Fama Cafè | Verona is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Verona.

Continue your lively evening at Archivio, a perfect place for winding down or revving up the night, depending on which mood you’re in. La Segreteria Café is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Grande Giove Cocktail Bar ensures a night out tailored to your taste.

Head back to your accommodation in Verona and get some rest in preparation for another magical day of your road trip in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Venice. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 2 nights.

Start by visiting Santa Maria Della Salute, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Peggy Guggenheim Collection, another must-visit landmark and interesting art gallery renowned for its awe-inspiring features.

While exploring and sightseeing, take time to savor the culture of Verona by sampling some local delicacies. When you’re ready for more sightseeing, head to Santa Maria Gloriosa Dei Frari. This historic church is an essential place to visit for anyone looking for the full Verona experience. We also recommend visiting Grand Canal, an increasingly popular street.

At the end of the day, you will drive to Venice, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat in Venice. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Bauer Hotel, a top-rated dining spot in Venice. If you're in the mood for something new, try L'Osteria Le Guglie, another premier location with a delectable menu. You might also want to book a table at Corner Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Venice.

Unwind after your meal by stepping into Al Parlamento. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, The Caffe Rosso offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Adagio, another top-rated bar in the area.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Day 6 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

Savor the day by visiting some of the best places to see in Venice, including a historical landmark, an opera house, a public square, a church, a palace, a monument and much more! Start your adventure at Rialto Bridge. This world-famous historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Teatro La Fenice located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Piazza San Marco. Its UNESCO world heritage-designated features will captivate you. After the public square, continue your tour of the city with a visit to St Mark's Basilica. Visitors usually appreciate the majestic features of this church. Next up is Doge's Palace, a highly recommended palace. For a change of pace, head to Bridge Of Sighs. As one of the most interesting attractions in Venice, this monument is the perfect place to end your self-guided sightseeing tour.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Venice's best restaurants.

Don’t miss out on dining at Generator Venice, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Nevodi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Il Mercante, a well-loved spot among locals and tourists. Or, head to The Irish Pub Venezia. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ai Stagneri, another top-rated place in the area.

Celebrate another amazing day of your road trip adventure in Italy!

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 3 nights.

Just a short distance away you'll find your next stop, Basilica Of Santa Croce In Florence, a culturally significant church that draws visitors from far and near.

Continue your journey to David, one of the city’s most popular spots that you shouldn’t miss. Another great site to visit is the popular Central Market. When you're finished at the food market, Cathedral Of Santa Maria Del Fiore awaits your visit. This church is a history-steeped highlight on today's itinerary.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Relax and recharge in preparation for another adventurous day in Italy!

Day 8 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in Florence by discovering the best things there are to see and do in the city.

Make sure to visit Oltrarno, a popular neighborhood in Florence. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Ponte Vecchio. This timeless historical landmark provides an insightful glimpse into the city's identity. Next, discover Piazza Della Signoria, a visually striking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Bargello National Museum, a frequently visited museum. When you’re done, don’t forget to make a stop at the well-known Palazzo Vecchio. Round off your day at Uffizi Gallery, another gem in Florence with picture-perfect features to discover.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

Get a good night's sleep and look forward to another great day on the road in Italy!

Greet day 9 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa.

Start by visiting Santa Maria Della Spina, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Knights' Square, another must-visit landmark and worthwhile public square renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Leaning Tower Of Pisa. This breathtaking monument is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Pisa Cathedral, a beloved church. Nearby, you'll also find Piazza Del Duomo, Pisa, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Campo Santo and wrap up your day with its historic appeal.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 1 night.

Florence is home to plenty of attractions that offer fun adventures, scenic views, and photo-friendly spots! Start at Porta Romana, a worthwhile monument that is worthwhile a visit in the city. Nearby, you’ll find Palazzo Salimbeni, enchanting visitors with its photogenic appeal. Continue your exploration at Basilica Of San Domenico. This church is one of the city’s most locally appreciated spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Siena Cathedral. After exploring the church, head to the underrated Pubblico Palace. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Del Campo, a place of visually striking interest in Florence.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 3 nights here for some well-deserved relaxation.

Get ready for a day filled with family-friendly attractions, breathtaking views, and photo-friendly spots in the charming city of Siena. Your adventure starts at Colosseum, a wondrous local hot spot. Another notable attraction to explore is Roman Forum. This wondrous archeological site is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Del Popolo. This visually striking public square offers a fascinating experience that many visitors find memorable. Capitoline Museums is also worth visiting.

At the end of the day, you will drive to Rome, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

On day 12 of your road trip in Italy, you’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 2 nights more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

Make sure to visit Trastevere, a popular neighborhood in Vatican City. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and photo-friendly spots. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Vatican Museums is the first of them. Sistine Chapel is your next stop. This extraordinary chapel is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit St. Peter's Basilica. To round off your sightseeing experience, visit Campo De' Fiori and Piazza Navona.

When you’re done exploring for the day, you’ll return to Rome and your accommodation.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Savor the flavors at RomAntica, a top pick for dinner tonight. Alternatively, Coso Ristorante beckons with its unique menu offerings. Also, consider DEROMA - Farine Romane. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Savor another day of unforgettable experiences in Italy!

Day 13 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Of San Clemente. This culturally significant church is sure to ignite your curiosity. Next, dive into the visually striking features of Spanish Steps, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Piazza Di Spagna, an iconic public square. For a change of scene, check out Trevi Fountain, known for its majestic features. We also recommend visiting Pantheon. This monument is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Castel Sant'angelo, yet another astonishing attraction in Rome.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

On day 14 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Bologna. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Today’s agenda in Rome includes a church, a public square, and a monument. Bologna Cathedral is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Maggiore, a widely recognized public square, located just a leisurely stroll away. Next, head to Two Towers, a historic monument, also available for your discovery today.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Let the evening flow smoothly from dinner to drinks at Bhangrabar, a top-rated bar in the area. For other recommendations, Rufus Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Ostello Bello Grande offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!